Acetone → 1,4-Dimethoxynaphthalene

HRID 1494388Notes

Reaction equation

HRID 1494388 reaction equation
[CH3:1]C(C)=O.O[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([OH:16])=[CH:8][CH:7]=1.[C:17](=[O:20])([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>O>[CH3:1][O:16][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([O:20][CH3:17])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 113051,4-NaphthalenediolHCID 11430Potassium Carbonate

Product 1

HCID 823371,4-Dimethoxynaphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To one liter of acetone were added 50.0 g (0.31 mol) of 1,4-dihydroxynaphthalene. To the resulting solution then were added 95.0 g (0.69 mol) of powdered potassium carbonate and 65 ml (0.69 mol) of dimethyl sulfate. The resulting mixture was stirred at reflux for 18 hours after which it was diluted with two liters of water and then extracted with methylene chloride. The organic extracts were combined,.dried over sodium sulfate, and evaporated in vacuo to give a black oil. The oil was distilled in vacuo to give 12.5 g of 1,4-dimethoxynaphthalene as an orange crystalline solid. b.p. 155° C. at 5 mm Hg.

Workup

  1. temperatureat reflux for 18 hours after which it
  2. extractionextracted with methylene chloride
  3. customevaporated in vacuo
  4. customto give a black oil
  5. distillationThe oil was distilled in vacuo

Sources & evidence

ORD record
ord-babb43ff329b486fac4eeb8b37be716f
Source dataset
uspto-grants-1991_06
Patent number
US05026707

Reaction notes

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